"Losing a best friend": The complicated relationship between Scott Disick and the Kardashian family.

Scott Disick wasn't really meant to be famous.

Or at least not the socialite and pop culture icon he is today. It kind of just... happened, as these things ever so rarely do. 

And it's all thanks to the Kardashians. 

Watch: The Kardashians trailer. Post continues after video. 

We were first introduced to Scott on season one of Keeping Up With The Kardashians, as Kourtney's boyfriend. After meeting in 2006 at a party thrown by the Girls Gone Wild creator Joe Francis, the pair quickly became an item. 

While they've been on and off for the last 15 years, there's no denying that Scott has firmly planted his roots in the Kardashian dynasty. 

However, while he may be here to stay, it doesn't mean that his relationship with the world's most famous family is simple. In fact, it has been complicated since Scott first stepped onto the set of KUWTK.

Here's why. 

What happened between Kourtney Kardashian and Scott Disick?

Kourtney and Scott's relationship was an uphill battle from the beginning. After meeting in 2006, they took us on their journey as they broke up, got back together, welcomed not one, not two, but three babies together and learned how to co-parent their kids without being a couple.

But before the peace, there was drama. A whole lot of it. 

In the season two premiere of KUWTK in March 2008, Kourtney and Scott had their first official falling out as a couple after she found a series of texts on his phone to another woman. 

By August 2009, they not only reconciled but also revealed that they were expecting their first child, Mason.

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A post shared by Scott Disick (@letthelordbewithyou)

While they attempted to make it work after the arrival of their son, KUWTK detailed a disastrous dynamic between the two as Scott's partying continued to spiral out of control. 

During an episode of Kourtney & Khloé Take Miami, he punched a mirror. While Kourtney immediately ended things, she later took him back. 

Kourtney and Scott, 2009. Image: Getty.

This pattern would follow the pair throughout the entirety of the Kardashian's three pregnancies until in 2015, when the pair decided end things for good. 

How Scott became a part of the Kardashian family.

Scott didn't always exactly get along with Kardash-Jenner clan. In fact, Khloé admits there was one point in time where she "hated him". 

In the earlier seasons of KUWTK, you'd be hard pressed to find a moment where Khloé and Scott got along. According to reports, she was constantly disgruntled by the way he treated her sister.

Kourtney shared a thoughtful message for Scott Disick on Fathers Day in 2020. "Thankful for you and these three special ones." Image: Kourtney Kardashian. 

Thankfully, by the late 2010s, Khloe and Scott became as close as ever, having buried the hatchet and turning over "a new leaf".

In a 2015 interview with Complex, she quipped that there had even been rumours she and Scott were "sleeping together", due to their close relationship.

"Obviously, we're best of friends, but what's crazy is how much I hated him before. He was a douchey little dick." 

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A post shared by Scott Disick (@letthelordbewithyou)

"At first I liked Scott. I wouldn’t say I loved him because Kourtney and I lived together in a townhouse when they met and Scott basically moved right on in. They didn’t really slowly progress. It was kind of full throttle and I liked him.

"We would hang out from time to time and then he started just acting out and doing stupid s**t and it was so consistent. You can say you’re sorry 5,000 times, but that doesn’t mean you mean it. He kept apologising, and I just started hating him for how much he was mistreating Kourtney. 

"I’m not going to keep accepting your apologies, letting you come back in, and doing the same thing over again."

She added, "He still falls off or makes mistakes, which everyone does. I don't expect anyone to be perfect, but what I like about Scott is that he's honest about his weaknesses and his strengths."

As for Kim Kardashian's stance on Scott, she revealed that she chose "peace" over starting arguments, saying during one episode: "I think regardless of Scott and Kourtney being together, Scott will always be in our lives."

Kim and Scott. Image: Instagram @KimKardashian.

"I mean, he's the father of my nephews and my niece. We want him healthy and happy, so that he can be in their lives as much as possible. But I still want Kourtney to figure it out and be strong and not get back together with him."

In 2013, Scott lost his mother, and then just a few months later, his father passed too. He admitted during the time that he was now without "a family".

"Losing my parents is not an easy subject for me to talk about," he admitted. "It puts me in a very vulnerable place, to remember them and think about them."

"I think when my parents passed, it was too hard to talk about," he said.

Kris Jenner was set on getting along with the father of three of her grandchildren, telling her oldest daughter in the last season of KUWTK: "Listen there's nothing that I would love more than to see you live your life and grow old with someone, be happy and content and peaceful," she said. 

"And it would always be so fabulous if it was the dad of your children, you know." 

Kris went on to say: "He fits well with all of us because we've all been around each other for so long I think. At this stage from what he tells me, he would love for it to be you and him."

Kourtney has since moved on with drummer Travis Barker. In October 2021, the pair got engaged.

For Travis, he revealed in 2021 that the couple had bonded over both being parents. 

"I’ve done both up until now. I would date girls that didn’t have kids and I find it kind of hard because I think they would have trouble understanding, [like] 'Why don’t you want to go to dinner every night?,'" he explained. 

"'Why don’t you want to see me every night?' Now I’m spending time with a woman who’s a great mom, who’s a great friend and you don’t have to worry about any of those things. 

"It just comes natural. It’s like a maturity thing."

During the first episode of The Kardashians, Kourtney also revealed she and Travis were trying for a baby. 

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A post shared by Kourtney ❤️ (@kourtneykardash)

A clip from the new show captured Kourtney explaining the IVF process had been difficult for her. She told Kris the treatment was not "amazing."

"Every single person on social media is always like 'Kourtney’s pregnant, Kourtney’s pregnant, Kourtney’s gained so much weight,'" she said in the clip. "It’s so rude to comment on people when you have no idea what they’re actually going through. The medication they’re giving me, they put me into menopause.… Literally into menopause."

While Scott has kept his romance on the down low after his last few relationships which lived in the public eye - he showed up to The Kardashians premier with model Rebecca Donaldson on his arm.

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What's life like now for Kourtney Kardashian and Scott Disick? 

While the pair have a complicated history, Kourtney has made it clear she has no intention to go backwards. 

"For so many years Scott always gotten away with bad behaviour and still been invited [to family events]," she said during the new season of The Kardashians. "And I don't think that's going to continue."

For Scott, he admitted the loss of both of his parents meant he is virtually unable to have a family - except for when he is invited to Kardashian events.

"It was a huge adjustment losing Kourtney romantically, but now it’s becoming a huge adjustment losing her [as a] best friend," he told Khloé after not being invited to a family BBQ.

"Now we’re really just more of co-parenters. I would say it’s probably one of the more difficult things in my life."

Scott ended the conversation by adding: “At the end of the day I understand what the bigger picture is, what would be best for Kourtney. She’s happy, she’s in a real thing and I believe that’s true.”

Feature Image: Getty / Instagram @Letthelordbewithyou.